Process of producing caoutchouc-like substances.



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PROCESS OF PRODUCING CAOUTCHOUG-LIEE SUBSTANCES.

Specification of Letters Patent.

Patented Aug. 12, 1913.

lo Drawing. Original applications filed August 24, 1910, Serial Ros. 578,607 and 578,608. Divided and this application filed February 21, 1912. Serial No. 679,081.

applications Serial Numbers 578,607 and 57 8,608, filed August 24, 1910.

We have found that by our novel method of polymerization hydrocarbons of the crythrene series such as erythrene itself,

on,=oH oH=oH,' and isoprene or beta-methyl-erythrene,

OH,=C (OH )OH=CH,,

which hydrocarbons contain the characteristic nucleus of the erythrene series, aphically represented C=CC=C, can e converted into caoutchouc-like substances in an eflicient manner, .and that the caoutchouclike substances thus obtained possess many of the valuable properties of natural caoutchouc.

The new process for producing the caout-v chouc-like substances consists in heating under caoutc'houc-forming conditions the hydrocarbon of the erythrene series, such as erythrene or isoprene, in an isolated and substantially pure condition, alone, or without material addition thereto of reagents such as acids, bases or diluent's until acaoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene. The heating is advantageously carried on in a confined space, or under pressure as in an autoclave. The hydrocarbon thus heated is polymerized, and converted in part or in whole into polymerization products, giving an etficient yield of the caoutchouclike polymerization product, together with more or less by-products, such as terpenes. The liquid may be stirred during the reaction to promote homogeneity. After the reaction has been carried to the desired stage emplified by the following specific examples of its application.

Example A: 200 parts of erythrene are liquefied by cooling, 6. 9., with a mixture of ether and solid or liquid carbonic acid. The resulting liquid is then heated in an autoclave for four days at from 90 to 100 C. Unchanged erythrene is removed and the residue is heated for some time in 'vacuo on the water bath, the temperature of which is finally brought to boiling. On distillation a liquid distils over, while the caoutchouclike product remains behind. 1

Example B: .100 parts of erythrene are heated in an autoclave for some time, c. 9., 3 months in an incubator. to about 35 C. The caoutchouc substance is isolated as above described.

Example 0: Isoprene is heated in an autoclave for 3 weeks at about 70 C. A jelly-like mass is thus obtained, which is heated on the water bath in vacuo and is then heated in 'vacuo in an oil bath at 130 C. The caoutchouc substance is then shaken with 10 times its quantity of ether for 24: hours. The ether is poured off and the residue is heated to 3040 C. in 'vacuo.

The caoutchouc-like substances resulting from the process of the present invention are white substances insoluble in acetone and alcohol but soluble in benzene, which form ozonids, nitrosites and brom-addition products, which are capable of being vulcanized and which form valuable substitutes for natural caoutchouc.

Our method of polymerization may also be applied to mixtures of erythrene orisoprene and other hydrocarbons of the erythrene series and of similar groups in various proportions, to form caoutchouc-like substances.

We claim:

1. The process of producing a caoutchouc like substance which comprises polymerizing isoprene by heating alone under caoutchouc forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in'benzene. I

2. The process of producing a caoutchouclike substance which comprises polymerizing isoprene by heating alone under pressure under caoutchouc forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene.

The process of producing a caoutchouc like substance which comprises polymerizing isoprene by heating alone in a confined space under caoutchouc forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene.

4. The process of produclng a caoutchouclike substance which comprises polymeriz-- ing isoprene by heating alone under caoutchouc-forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene and isolating the caoutchouc like substance from the resulting product.

5. The process of producing a caoutchouc like substance which comprises polymerizing isoprene by heating alone under caoutchouc-forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble inbenezene. and removing volatile constituents from the resulting product by distillation.

6. The process of producing a caoutchouclike substance which comprises polymerizing isoprene by heating alone under caoutchouc-forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol butsoluble in benzene, and removing volatile constituents from the resulting product by distillation in cum.

7 The process of producing a caoutchouc like substance which comprises polymerizing a hydrocarbon of the erythrene series by heating alone under caoutchouc forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene.

8. The process of producing a caoutchouclike substance which comprises polymerizing a hydrocarbon of the erythrene series by heating alone under pressure under caoutchouc forming conditions'until a .caoutchouc-like product results insoluble in -acetone and alcohol butsoluble in benzene.

9. The process of producing a caoutchouclike substance which comprises polymerizing a hydrocarbon of the erythrene series by heating alone in a confined space under cauotchouc forming conditions until a caoutchouc-like product results insoluble in acetone and alcohol but soluble in benzene.

In testimony ,whereof we have hereunto set our hands in the presence of two subscribing Witnesses.

FRITZ HOFMANN. CARL COUTELLE. Witnesses:

HELEN NUFER, ALBERT NUFER. 

